# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Mar 23 13:08:45 2022
#   Inital geometry file: a 114 line input string
#   Ligand name: ~{N}4-cyclopropyl-~{N}2-methyl-6-[(1~{S})-1-phenylethyl]pyridine-2,4-dicarboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CNC(=O)c1cc(cc(n1)[C@@H](C)c2ccccc2)C(=O)NC3CC3
#
data_comp_list
loop_
_chem_comp.id
_chem_comp.three_letter_code
_chem_comp.name
_chem_comp.group
_chem_comp.number_atoms_all
_chem_comp.number_atoms_nh
_chem_comp.desc_level
_chem_comp.initial_date
_chem_comp.modified_date
_chem_comp.source
 ULE  ULE  ~{N}4-cyclopropyl-~{N}2-methyl-6-[(1~{S})-1-phenylethyl]pyridine-2,4-dicarboxamide  ligand  45  24  .  2022-08-11  2023-02-15
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_ULE
loop_
_chem_comp_atom.comp_id
_chem_comp_atom.atom_id
_chem_comp_atom.type_symbol
_chem_comp_atom.type_energy
_chem_comp_atom.charge
_chem_comp_atom.partial_charge
_chem_comp_atom.x
_chem_comp_atom.y
_chem_comp_atom.z
 ULE  N1   N  N     0  -0.456  41.4933  17.5215   8.4805
 ULE  C4   C  CR6   0   0.085  44.1484  17.3916   9.2454
 ULE  C5   C  CR16  0  -0.346  43.2482  18.2005   9.9193
 ULE  C6   C  CR6   0   0.304  41.9152  18.2341   9.5122
 ULE  C7   C  CH1   0  -0.409  40.9109  19.0737  10.2676
 ULE  C8   C  CH3   0  -0.640  39.7473  19.5417   9.3965
 ULE  C10  C  CR16  0  -0.325  40.5783  18.8447  12.7610
 ULE  C13  C  CR16  0  -0.237  39.3282  16.3923  12.4590
 ULE  C15  C  C     0   0.537  45.5844  17.3944   9.6856
 ULE  C17  C  CH2   0  -0.514  48.1521  14.8246  10.2694
 ULE  O1   O  O     0  -0.463  46.0688  18.3814  10.2140
 ULE  N2   N  NH1   0  -0.653  46.2701  16.2619   9.4648
 ULE  C16  C  CH1   0  -0.080  47.6582  16.1437   9.7743
 ULE  C18  C  CH2   0  -0.480  48.0847  15.9947  11.2013
 ULE  C3   C  CR16  0  -0.360  43.6893  16.6515   8.1600
 ULE  C2   C  CR6   0   0.125  42.3521  16.7558   7.8189
 ULE  C1   C  C     0   0.532  41.8224  15.9835   6.6415
 ULE  O    O  O     0  -0.478  42.5554  15.2709   5.9685
 ULE  N    N  NH1   0  -0.636  40.5191  16.1453   6.4120
 ULE  C    C  CH3   0  -0.515  39.8332  15.4870   5.3283
 ULE  C9   C  CR6   0   0.163  40.4220  18.3141  11.4848
 ULE  C14  C  CR16  0  -0.291  39.7923  17.0781  11.3462
 ULE  C12  C  CR16  0  -0.269  39.4860  16.9321  13.7301
 ULE  C11  C  CR16  0  -0.237  40.1133  18.1607  13.8780
 ULE  H1   H  HCR6  0   0.275  43.5689  18.8015  10.7602
 ULE  H2   H  HCH1  0   0.272  41.4431  19.9595  10.6259
 ULE  H3   H  HCH3  0   0.238  39.1098  20.2180   9.9657
 ULE  H4   H  HCH3  0   0.235  40.1065  20.0783   8.5178
 ULE  H5   H  HCH3  0   0.233  39.1335  18.7092   9.0556
 ULE  H6   H  HCR6  0   0.250  41.0681  19.8036  12.8845
 ULE  H7   H  HCR6  0   0.252  38.8419  15.4332  12.3343
 ULE  H9   H  HCH2  0   0.261  49.1194  14.4902   9.9195
 ULE  H10  H  HNH1  0   0.413  45.8091  15.4671   9.0512
 ULE  H11  H  HCH1  0   0.272  48.3174  16.7050   9.1198
 ULE  H12  H  HCH2  0   0.256  47.3094  15.9909  11.9561
 ULE  H13  H  HCH2  0   0.256  49.0059  16.4757  11.5025
 ULE  H14  H  HCR6  0   0.276  44.3432  16.0276   7.5661
 ULE  H15  H  HNH1  0   0.409  40.0100  16.7628   7.0254
 ULE  H16  H  HCH3  0   0.252  38.7819  15.7557   5.3723
 ULE  H17  H  HCH3  0   0.240  40.2256  15.7922   4.3574
 ULE  H18  H  HCH3  0   0.240  39.9138  14.4020   5.4025
 ULE  H19  H  HCR6  0   0.250  39.6648  16.6444  10.3611
 ULE  H20  H  HCR6  0   0.253  39.1235  16.3967  14.5981
 ULE  H21  H  HCR6  0   0.253  40.2433  18.5902  14.8633
 ULE  H8   H  HCH2  0   0.260  47.4252  14.0328  10.4029

loop_
_chem_comp_bond.comp_id
_chem_comp_bond.atom_id_1
_chem_comp_bond.atom_id_2
_chem_comp_bond.type
_chem_comp_bond.value_dist
_chem_comp_bond.value_dist_esd
_chem_comp_bond.value_dist_neutron
 ULE  C    N    single    1.442  0.020  1.442
 ULE  O    C1   double    1.224  0.020  1.224
 ULE  N    C1   single    1.333  0.020  1.333
 ULE  C1   C2   single    1.504  0.020  1.504
 ULE  C2   C3   aromatic  1.384  0.020  1.384
 ULE  C2   N1   aromatic  1.327  0.020  1.327
 ULE  C3   C4   aromatic  1.392  0.020  1.392
 ULE  N1   C6   aromatic  1.323  0.020  1.323
 ULE  C8   C7   single    1.527  0.020  1.527
 ULE  C4   C15  single    1.502  0.020  1.502
 ULE  C4   C5   aromatic  1.385  0.020  1.385
 ULE  C6   C5   aromatic  1.394  0.020  1.394
 ULE  C6   C7   single    1.511  0.020  1.511
 ULE  C17  C16  single    1.493  0.020  1.493
 ULE  C17  C18  single    1.497  0.020  1.497
 ULE  N2   C15  single    1.342  0.020  1.342
 ULE  N2   C16  single    1.427  0.020  1.427
 ULE  C15  O1   double    1.220  0.020  1.220
 ULE  C16  C18  single    1.497  0.020  1.497
 ULE  C7   C9   single    1.516  0.020  1.516
 ULE  C14  C9   aromatic  1.394  0.020  1.394
 ULE  C14  C13  aromatic  1.387  0.020  1.387
 ULE  C9   C10  aromatic  1.391  0.020  1.391
 ULE  C13  C12  aromatic  1.390  0.020  1.390
 ULE  C10  C11  aromatic  1.390  0.020  1.390
 ULE  C12  C11  aromatic  1.387  0.020  1.387
 ULE  C5   H1   single    0.930  0.020  1.080
 ULE  C7   H2   single    0.970  0.020  1.090
 ULE  C8   H3   single    0.970  0.020  1.090
 ULE  C8   H4   single    0.970  0.020  1.090
 ULE  C8   H5   single    0.970  0.020  1.090
 ULE  C10  H6   single    0.930  0.020  1.080
 ULE  C13  H7   single    0.930  0.020  1.080
 ULE  C17  H8   single    0.970  0.020  1.090
 ULE  C17  H9   single    0.970  0.020  1.090
 ULE  N2   H10  single    0.860  0.020  1.020
 ULE  C16  H11  single    0.970  0.020  1.090
 ULE  C18  H12  single    0.970  0.020  1.090
 ULE  C18  H13  single    0.970  0.020  1.090
 ULE  C3   H14  single    0.930  0.020  1.080
 ULE  N    H15  single    0.860  0.020  1.020
 ULE  C    H16  single    0.970  0.020  1.090
 ULE  C    H17  single    0.970  0.020  1.090
 ULE  C    H18  single    0.970  0.020  1.090
 ULE  C14  H19  single    0.930  0.020  1.080
 ULE  C12  H20  single    0.930  0.020  1.080
 ULE  C11  H21  single    0.930  0.020  1.080

loop_
_chem_comp_angle.comp_id
_chem_comp_angle.atom_id_1
_chem_comp_angle.atom_id_2
_chem_comp_angle.atom_id_3
_chem_comp_angle.value_angle
_chem_comp_angle.value_angle_esd
 ULE  C2   N1   C6   119.54  3.000
 ULE  C3   C4   C15  123.03  3.000
 ULE  C15  C4   C5   118.53  3.000
 ULE  C3   C4   C5   118.39  3.000
 ULE  H1   C5   C6   119.79  3.000
 ULE  H1   C5   C4   120.64  3.000
 ULE  C6   C5   C4   119.57  3.000
 ULE  C7   C6   C5   120.19  3.000
 ULE  C7   C6   N1   118.49  3.000
 ULE  C5   C6   N1   121.31  3.000
 ULE  H2   C7   C9   107.44  3.000
 ULE  H2   C7   C8   108.03  3.000
 ULE  C9   C7   C8   111.47  3.000
 ULE  H2   C7   C6   106.87  3.000
 ULE  C9   C7   C6   109.71  3.000
 ULE  C8   C7   C6   113.05  3.000
 ULE  H5   C8   H4   108.04  3.000
 ULE  H5   C8   H3   107.95  3.000
 ULE  H4   C8   H3   107.95  3.000
 ULE  H5   C8   C7   111.95  3.000
 ULE  H4   C8   C7   111.07  3.000
 ULE  H3   C8   C7   109.75  3.000
 ULE  H6   C10  C11  119.67  3.000
 ULE  H6   C10  C9   119.53  3.000
 ULE  C11  C10  C9   120.81  3.000
 ULE  H7   C13  C12  120.02  3.000
 ULE  H7   C13  C14  119.73  3.000
 ULE  C12  C13  C14  120.24  3.000
 ULE  N2   C15  O1   123.44  3.000
 ULE  O1   C15  C4   120.54  3.000
 ULE  N2   C15  C4   116.02  3.000
 ULE  H9   C17  H8   114.46  3.000
 ULE  H9   C17  C18  118.89  3.000
 ULE  H8   C17  C18  117.66  3.000
 ULE  H9   C17  C16  117.50  3.000
 ULE  H8   C17  C16  117.69  3.000
 ULE  C18  C17  C16   60.07  3.000
 ULE  H10  N2   C16  117.95  3.000
 ULE  H10  N2   C15  119.96  3.000
 ULE  C16  N2   C15  122.08  3.000
 ULE  H11  C16  C18  116.96  3.000
 ULE  H11  C16  N2   114.66  3.000
 ULE  C18  C16  N2   119.48  3.000
 ULE  H11  C16  C17  117.13  3.000
 ULE  C18  C16  C17   60.11  3.000
 ULE  N2   C16  C17  117.83  3.000
 ULE  H13  C18  H12  114.67  3.000
 ULE  H13  C18  C16  117.63  3.000
 ULE  H12  C18  C16  117.47  3.000
 ULE  H13  C18  C17  118.83  3.000
 ULE  H12  C18  C17  117.63  3.000
 ULE  C16  C18  C17   59.82  3.000
 ULE  H14  C3   C2   119.49  3.000
 ULE  H14  C3   C4   122.39  3.000
 ULE  C2   C3   C4   118.10  3.000
 ULE  C1   C2   C3   119.63  3.000
 ULE  C3   C2   N1   123.08  3.000
 ULE  C1   C2   N1   117.29  3.000
 ULE  N    C1   O    124.16  3.000
 ULE  N    C1   C2   114.62  3.000
 ULE  O    C1   C2   121.22  3.000
 ULE  H15  N    C    119.78  3.000
 ULE  H15  N    C1   117.59  3.000
 ULE  C    N    C1   122.62  3.000
 ULE  H18  C    H17  108.21  3.000
 ULE  H18  C    H16  108.36  3.000
 ULE  H17  C    H16  108.37  3.000
 ULE  H18  C    N    111.59  3.000
 ULE  H17  C    N    111.72  3.000
 ULE  H16  C    N    108.49  3.000
 ULE  C14  C9   C10  118.70  3.000
 ULE  C10  C9   C7   120.62  3.000
 ULE  C14  C9   C7   120.68  3.000
 ULE  H19  C14  C9   119.88  3.000
 ULE  H19  C14  C13  119.47  3.000
 ULE  C9   C14  C13  120.65  3.000
 ULE  H20  C12  C11  120.27  3.000
 ULE  H20  C12  C13  120.21  3.000
 ULE  C11  C12  C13  119.52  3.000
 ULE  H21  C11  C12  120.17  3.000
 ULE  H21  C11  C10  119.74  3.000
 ULE  C12  C11  C10  120.09  3.000

loop_
_chem_comp_tor.comp_id
_chem_comp_tor.id
_chem_comp_tor.atom_id_1
_chem_comp_tor.atom_id_2
_chem_comp_tor.atom_id_3
_chem_comp_tor.atom_id_4
_chem_comp_tor.value_angle
_chem_comp_tor.value_angle_esd
_chem_comp_tor.period
 ULE  CONST_01  C4   C3   C2   N1     0.00   0.0  0
 ULE  CONST_02  C4   C5   C6   N1     0.00   0.0  0
 ULE  CONST_03  C2   C3   C4   C5     0.00   0.0  0
 ULE  CONST_04  C2   N1   C6   C5     0.00   0.0  0
 ULE  CONST_05  C3   C2   N1   C6     0.00   0.0  0
 ULE  CONST_06  C3   C4   C5   C6     0.00   0.0  0
 ULE  CONST_07  C13  C14  C9   C10    0.00   0.0  0
 ULE  CONST_08  C13  C12  C11  C10    0.00   0.0  0
 ULE  CONST_09  C12  C13  C14  C9     0.00   0.0  0
 ULE  CONST_10  C12  C11  C10  C9     0.00   0.0  0
 ULE  CONST_11  C11  C10  C9   C14    0.00   0.0  0
 ULE  CONST_12  C11  C12  C13  C14    0.00   0.0  0
 ULE  CONST_13  C1   C2   C3   C4   180.00   0.0  0
 ULE  CONST_14  C7   C6   C5   C4   180.00   0.0  0
 ULE  CONST_15  C1   C2   N1   C6   180.00   0.0  0
 ULE  CONST_16  C15  C4   C5   C6   180.00   0.0  0
 ULE  CONST_17  C2   N1   C6   C7   180.00   0.0  0
 ULE  CONST_18  C13  C14  C9   C7   180.00   0.0  0
 ULE  CONST_19  C11  C10  C9   C7   180.00   0.0  0
 ULE  CONST_20  C2   C3   C4   C15  180.00   0.0  0
 ULE  CONST_21  H14  C3   C2   N1   180.00   0.0  0
 ULE  CONST_22  H1   C5   C6   N1   180.00   0.0  0
 ULE  CONST_23  H19  C14  C9   C10  180.00   0.0  0
 ULE  CONST_24  H20  C12  C11  C10  180.00   0.0  0
 ULE  CONST_25  H21  C11  C12  C13  180.00   0.0  0
 ULE  CONST_26  H7   C13  C14  C9   180.00   0.0  0
 ULE  CONST_27  H6   C10  C9   C14  180.00   0.0  0
 ULE  CONST_28  C16  N2   C15  C4   180.00   0.0  0
 ULE  CONST_29  C16  N2   C15  O1     0.00   0.0  0
 ULE  CONST_30  C    N    C1   C2   180.00   0.0  0
 ULE  CONST_31  H10  N2   C15  C4     0.00   0.0  0
 ULE  CONST_32  H15  N    C1   C2     0.00   0.0  0
 ULE  CONST_33  C    N    C1   O      0.00   0.0  0
 ULE  Var_01    N2   C16  C18  C17  107.08  30.0  1
 ULE  Var_02    O    C1   C2   N1   178.91  30.0  2
 ULE  Var_03    N2   C15  C4   C5   151.71  30.0  2
 ULE  Var_04    C17  C16  N2   C15  144.76  30.0  3
 ULE  Var_05    H16  C    N    C1   178.32  30.0  3

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 ULE  chir_01  C7   C8   C6  C9   positiv
 ULE  chir_02  C16  C17  N2  C18  both

loop_
_chem_comp_plane_atom.comp_id
_chem_comp_plane_atom.plane_id
_chem_comp_plane_atom.atom_id
_chem_comp_plane_atom.dist_esd
 ULE  plan-1  N1   0.020
 ULE  plan-1  C4   0.020
 ULE  plan-1  C5   0.020
 ULE  plan-1  C6   0.020
 ULE  plan-1  C7   0.020
 ULE  plan-1  C15  0.020
 ULE  plan-1  C3   0.020
 ULE  plan-1  C2   0.020
 ULE  plan-1  C1   0.020
 ULE  plan-1  H1   0.020
 ULE  plan-1  H14  0.020
 ULE  plan-2  C7   0.020
 ULE  plan-2  C10  0.020
 ULE  plan-2  C13  0.020
 ULE  plan-2  C9   0.020
 ULE  plan-2  C14  0.020
 ULE  plan-2  C12  0.020
 ULE  plan-2  C11  0.020
 ULE  plan-2  H6   0.020
 ULE  plan-2  H7   0.020
 ULE  plan-2  H19  0.020
 ULE  plan-2  H20  0.020
 ULE  plan-2  H21  0.020
 ULE  plan-3  C2   0.020
 ULE  plan-3  C1   0.020
 ULE  plan-3  O    0.020
 ULE  plan-3  N    0.020
 ULE  plan-3  C    0.020
 ULE  plan-3  H15  0.020
 ULE  plan-4  C4   0.020
 ULE  plan-4  C15  0.020
 ULE  plan-4  O1   0.020
 ULE  plan-4  N2   0.020
 ULE  plan-4  C16  0.020
 ULE  plan-4  H10  0.020

